Methanol → HCID 21449337, compound

Participants

Reaction Steps

To a solution of anhydrous 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid (1.0g.) in ethanol-free chloroform (30 ml; dried over calcium chloride) was added a solution of thionyl chloride (0.19 ml.) in chloroform (2ml). The resulting dark red solution was stirred at room temperature for 30 mins., and then methanol (20 ml.) was added. The mixture was heated under reflux for 30 mins., saturated sodium acetate solution (2 ml.) was added, and the mixture was concentrated in vacuo. Water (30 ml.) was added to the residue and the mixture was extracted with ether (3 × 30 ml.). The ether extracts were washed successively with saturated sodium hydrogen carbonate solution (30 ml.) and water (30 ml.), and dried (Na2SO4). Evaporation of the solvent gave a dark yellow oil, which slowly crystallised to give methyl 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate, m.p. 112°-114° C.

Provenance & Evidence